Boston Bruins win Stanley Cup

The 1939 Stanley Cup Final NHL championship series was contested by the Boston Bruins and the Toronto Maple Leafs.

It was Boston's first appearance in the Final since 1930; Toronto had appeared in the 1938 Final. Boston would win the series 4–1 to win their second Stanley Cup. It was the first best-of-seven Stanley Cup Final series.

The Boston Bruins finished in first during the regular season, with goaltender Frank Brimsek finishing with a spectacular 1.59 goals-against average. Chicago, who had won the Stanley Cup the previous season, finished in last place in 1938-39 and missed the playoffs. Boston faced the Rangers to decide which of the two would participate in the Stanley Cup final. It took seven rough and tumble games, but the Bruins prevailed. The other qualifying rounds saw Toronto eliminate the Americans in two games, while the Red Wings edged the Canadiens two games to one to take their series. Subsequently, the Maple Leafs won the best of three over Detroit two games to won to win passage to the Stanley Cup final against the Bruins. For the first time, the final was to be a best of seven competition. Led by Roy Conacher's five goals, Boston beat Toronto four games to one to win the Stanley Cup for the first time since 1928-29.

The 1938–39 Boston Bruins season was the Bruins' 15th season in the NHL, and they were coming off of a very successful regular season in 1937–38, winning the American Division with a record of 30–11–7, however, they lost to the Toronto Maple Leafs in the Stanley Cup semi-finals. This season, the Bruins would meet the Maple Leafs in a rematch, and win the series 4–1 to win the Stanley Cup for the second time, and the first time in 10 years.

In the playoffs, Boston would have a 1st round bye, advancing straight to the NHL semi-finals, where they would face the 2nd place New York Rangers in a best of 7 series. New York had 58 points during the regular season, which was 16 less than the Bruins. The series opened at Madison Square Garden in New York, and the Bruins would win a thrilling, triple overtime game by a score of 2–1. Game 2 moved to the Boston Garden, and Boston took a 2–0 series lead with a 3–2 overtime victory. The Bruins took a commanding 3–0 lead in the series with a 4–1 win, looking to close out the series in the 4th game, as the series shifted back to New York. The Rangers would hold off elimination, defeating Boston 2–1, and then in game 5 in Boston, the game would be decided in overtime, with New York once again winning by a 2–1 score to cut the series lead to 3–2. Game 6 was played back in New York, and the Rangers easily defeated the Bruins 3–1, to tie the series up at 3 games, forcing a 7th game to be played in Boston. The game would be tied 1–1 after regulation time, and would not be settled until the 3rd overtime period, when Boston finally snapped the tie, winning the game 2–1, and taking the series 4–3, to advance to the Stanley Cup finals.
The Bruins opponent was the Toronto Maple Leafs, who finished the season with a 19–20–9 record, earning 47 points, which was 27 points fewer than Boston. The Leafs defeated the New York Americans and Detroit Red Wings to earn a spot in the best of seven finals. The series would begin with 2 games in Boston, and each team won a game, as the series moved to Maple Leaf Gardens for games three and four. Boston would take control in Toronto, winning game three by a 3–1 score, then shutting out the Leafs 2–0 in game four, to take a 3–1 series lead. Boston then returned home for game five, and defeated Toronto 3–1, to win their first Stanley Cup in 10 years, and second in team history.